Ethylparaben → HCID 65018987, compound

HRID 2261221Notes

Reaction equation

HRID 2261221 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.O[CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:17]1[CH2:18][CH2:19][CH:14]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 65018987HCID 65018987, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ice-cold solution of ethyl 4-hydroxybenzoate (0.82 g), 4-hydroxy-tetrahydro-2H-pyran (0.5 g) and triphenylphosphine in THF (50 ml) was treated dropwise with diisopropyl azodicarboxylate (1.69 ml). After 15 min the cooling bath was removed and the reaction stood overnight at rt. The mixture was evaporated, redissolved in toluene and successively washed with 2N sodium hydroxide (2×20 ml), water (2×20 ml) and brine (20 ml). After drying (magnesium sulfate) the solution was loaded directly on to a silica flash column (step gradient 10-30% EtOAc in light petroleum 40-60) to give the title compound (D5) (0.75 g). 1H NMR δ (CDCl3): 7.98 (2H, d, J=8.5Hz), 6.91 (2H, d, J=8.5 Hz), 4.60 (1H, m), 4.35 (2H, q, J=9.8 Hz), 3.98 (2H, m), 3.57 (2H, m), 2.05 (2H, m), 1.80 (2H, m), 1.38 (3H, t, J=9.8 Hz).

Workup

  1. customAfter 15 min the cooling bath was removed
  2. customThe mixture was evaporated
  3. dissolutionredissolved in toluene
  4. washsuccessively washed with 2N sodium hydroxide (2×20 ml), water (2×20 ml) and brine (20 ml)
  5. dry with materialAfter drying (magnesium sulfate) the solution

Sources & evidence

ORD record
ord-d8a1df2603954e71945435b58964bb22
Source dataset
uspto-grants-2010_12
Patent number
US07846922B2

Reaction notes

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